You Deserve Better

Ben pulled up to the valet and took a deep breath before he got out of the car. I watched him try to walk confidently in the unfamiliar shoes as she came around to open my door. He only stumbled once. I was so proud of him.

The valet drivers snickered, and I smiled at them and winked as I squeezed Ben's ass possessively. It amused me to see at least one expression turn from derision to thoughtful jealousy. Well, Ben had more boldness than the three of them put together. I hoped they recognized that. I hoped Ben recognized that.

I eyed him as we were led to our table. His expression was unreadable, caught somewhere between pride, fear, and pure animal arousal. His eyes caught mine, and I smiled at him. Someone had obviously instilled a sense of old-fashioned values in him somewhere along the line because he conscientiously pulled out my chair at the table when we arrived there.

Before sitting down, I reached up and pulled his head down to mine, kissing him with my tongue probing past his lips. He'd earned a reward, and I hoped he enjoyed that public claiming.

I sat down as Ben hurried to push the chair in under my rapidly lowering ass. When he sat across from me, I was pleased to see that much of the fear I'd noted seemed to be gone from his countenance.

"Have you ever been here?" I asked as I opened up the menu.

Ben shook his head.

"You should try the steak," I suggested, driven by a desire to see him eating that most masculine of meals while trying to avoid getting his dress dirty. I loved that juxtaposition of the male and female, the harsh and delicate, the confidence and submission.

I pictured him, with legs crossed daintily, cock cage pressed between his muscular thighs, slugging down a whiskey and smoking a cigar. Mmmm... And then I'd bend him over and fuck him with a strap-on as he desperately tried to hold onto some semblance of his male identity. My brain happily amped up the humiliation factor for me, supplying an imaginary cock for Ben to suck as I pegged him. I was so distracted by my wandering imagination that the arrival of the waiter to take our orders caught me entirely off guard.

The waiter didn't react at all to Ben's outfit, obviously much more of a professional than the valet drivers. Ben obediently ordered a steak, and I asked for a pasta dish. When the waiter left, Ben, following his instructions to be confident, examined my face. I smirked as I saw his hand raise ever so hesitantly from the table, enough for me to notice, but not sufficient to draw attention from other diners.

I considered ignoring him until he raised it as high as an excited 5th grade brown-noser, but I relented.

"Yes, Ben?" I called on him.

"May I ask what you were thinking about, Ma'am?"

"I was imagining fucking your ass in that dress, Ben," I answered bluntly.

Ben's cheeks flushed, which I really appreciated. It made it so much easier to see when I'd struck a nerve with him.

"And then I imagined you sucking cock while I did it, spit roasted."

"Oh," Ben said quietly.

I leaned in and asked in a lusty tone, "Would you like that?"

Slowly, ever so slowly, Ben nodded.

I leaned back and smiled, "Consider tonight a date, Ben. Talk to me about your life, your desires, your dreams for the future. Tell me everything."

Ben stared at me for a moment, nodded a little, lifted his hand as if to raise it, then carefully set it back down again. Yes, it was hard to adjust to new rules, and I really appreciated his efforts to fit his behavior to each situation I thrust on him. He was a smart guy, driven, ambitious; he had to be to be a PhD student in a STEM field. So, I had no doubt his brain could handle the complexities of the situation he now found himself in. He'd asked for it, after all.

"Will you tell me about you?" Ben asked his question.

"If you earn it," I said. "If you tell me something personal and true and meaningful, then you'll get the same in return."

Ben thought for a moment, considering where to start, "I was raised by a single mother, my dad died when I was four and my mom never re-married. She was a tough woman, she had to be when she had no more than a 10th grade education and had to take care of myself and herself and clean up the mess my dad left behind when he died.

"She got a job in fast food and a GED, then worked her way up to being a manager, then got a degree in nursing. She's a nursing supervisor now."

Ben paused and looked at me as if he expected me to share now.

"That's a nice story about your mom, Ben, but I wanted to hear about you," I pointed out.

The waiter delivered our meals at that moment, and Ben was quiet for a bit as he cut into his steak. His red dress shifted across his chest as he sliced through his rare meat. I twirled my pasta and watched him, arousal pulsing through my clit. I wondered if his cock was still pressed hard into his cage or if it had softened now.

Finally, Ben started again, "I remember the first time I wanted to be used. I had a crush on a woman who worked at an auto parts store. I knew she got a bit of commission on every sale, and I found myself spending more and more money on things I didn't need, just to see the smile that lit up her face.

"Eventually, I worked up the courage to ask her out, and she agreed. I was excited, but when I asked her any question about what she wanted or needed, she could never tell me. I wanted so much to give her things and serve her, but I couldn't guess at what it was that would make her happy.

"After a while, I realized I needed more than smiles. I need direction, guidance, clear communication, expectations. I want to feel useful."

I smiled with approval, "Good story. Here's one for you. I remember the first time I learned that I like to be obeyed. I was dating this guy, he was a bit of a disaster in his personal life. I was in college, pursuing a career, he was older than me, but still living off his parents' money. His apartment was a disaster, a complete mess.

"One day I got fed up with it and ordered him to clean. I remember the look in his eyes as he obeyed me. He was like a man who'd been shown a reason to make an effort, and he craved it. I sat and watched as he cleaned, instructing him on how to do it better, and I felt powerful. It wasn't just power, it was making someone change themselves for the better. I loved that feeling."

"Will you change me for the better?" Ben asked, boldly.

I smiled at him, "I'm going to push all your boundaries and limits, boy. I'm going to explore things with you that terrify and exhilarate you, if you'll let me. And it will change you. You'll know, then, who you are and what that means."

"I want to please you, Ma'am. I want to serve you, will you let me give you pleasure?"

"Just do as your told, Ben, and I'll be pleased."

Ben nodded and chewed his steak thoughtfully.

I slipped off my shoe and raised my foot to press onto the seat of his chair, inching my toes up to feel his cock cage, easily accessible under his dress as he sat with his legs spread wide. Ben jumped as he felt my foot touch him, brushing over his balls and kneading them with spread toes.

Ben's hand raised reflexively and I pressed firmly into his balls with my foot, "There's no need for that tonight, remember?"

"Yes Ma'am," Ben agreed with a wince, "Ma'am, may I touch your foot?"

"No."

Ben looked pained, "I give very good foot massages, Ma'am."

"Not tonight, you don't."

Ben's shoulders slumped cutely, "Yes, Ma'am."

I ordered dessert and allowed Ben to feed me scoops of ice cream while I fondled his balls with my toes. It was fun to watch him try to focus on aiming at my mouth properly as I worked to distract him. It took a bit of work, but I finally managed to make him slip and touch the ice cream to my cheek by mistake. Grinning, I pressed my foot into his balls with what I hoped was painful pressure. Ben's gasping wince seemed to indicate that I'd succeeded in my goal.

It probably wasn't fair to punish him for something I'd caused. But, I wasn't concerned with fairness at the moment. I was concerned with asserting dominance over my new submissive boy, dominance that he craved and which I could provide.

After dinner, I programmed the GPS and got into the backseat again. I pulled out one last shopping bag from where I'd stored it and prepared myself. Ben pulled to a stop in the gravel lot of the secluded park and waited. I wondered how hard it was for him to not ask questions in this moment.

I sat for a while and said nothing, letting the tension build. Well, I hoped it was tension and not boredom. I thought about that careful balance for a bit as I watched Ben's profile in the darkened front of the car.

Finally, I spoke, "Well, aren't you going to open my door for me?"

Ben jerked, taken aback at the implication that he'd been remiss in his duties. He lurched out of the front seat and came around to open my door. I stepped out, my new accessory obvious, even in the dim light of the moon.

I saw Ben's eyes widen as he locked his eyes on my new cock. It was the smallest one the store carried, but even that was larger than the average penis. Not as big as Ben's cock had been, when it was free, though.

"I think a punishment is in order, don't you? Because you had to be reminded to open my door, hmm?"

Quietly, Ben nodded.

"And, we're in private now, aren't we? Why aren't you in the position I taught you?"

Ben quickly adjusted his stance, legs open, hands clasped behind his hips.

"Then, after the punishment, a little reward for trying something new today," I stroked my plastic cock thoughtfully, "I've heard wonderful things about prostate glands. I think you should appreciate my willingness to stimulate it for you, no?"

Ben nodded.

"Turn around, hands against the car," I ordered, feeling a thrill tingle through me as Ben obeyed.

I pulled his dress up, revealing his pale butt.

"Have you ever been spanked?" I asked.

Ben nodded his head.

"Tell me how many hits you think you earned tonight?' I asked.

"Thr... Five?" Ben replied tentatively.

"It'll be eight then," I said with bravado I didn't really feel.

I'd only spanked someone once, the last time I'd tried out my dominance in the world of BDSM. The guy had been unhappy, I'd been disappointed, and that had been the last time I'd tried delivering on this particular fetish, regardless of my lingering desire. Well, there was no time like the present to try again.

I bit my lip as I lined up my hand, then I swung it back and down again onto Ben's soft flank. He barely reacted, so I figured I'd been too soft, despite the fact that my hand stung and buzzed from the impact.

"Count," I said, wanting to hear the effect of my slaps on his voice.

"One," Ben said, voice strong.

I aimed for the same spot again, trying to really get my whole body into it this time. I wished I'd thought to bring along a tool like a paddle or a cane. I cursed my lack of forethought on this point as my hand throbbed after smacking Ben's ass. Though, I noted with satisfaction that his knees buckled a bit and he gasped as he counted.

"Two."

This time Ben's butt clenched as I started my swing. That was a mistake, it was going to hurt more for him. I grimaced as my hand made contact, and it would hurt more for me too, I realized.

"Three."

I wished I'd amended the count to three, but then I caught sight of the pink blush on Ben's ass and a surge of desire to smack him again boiled up with me. Barely even pausing this time, I let go with an excited smack.

"Four," Ben gasped, his ass turning red as I watched.

It was time to attend to the other cheek now, I decided. I rained three blows down in succession, barely feeling the pain in my hand, driven away by the adrenalin of this matchup of wills.

"Five. Six. Seven."

On the seventh hit, Ben's legs gave way and he dropped a bit before regaining his stability and position. Both cheeks were rosy and red and a cruel thought occurred to me. Ben's legs were spread wide open, letting his caged cock dangle free, and his balls.

I aimed one last hard smack, and let go, slamming my hand into Ben's balls.

"Eight," Ben choked and gasped.

My pussy was on fire with arousal and I was grinning like a loon. I pulled the lube I'd purchased out of my pocket and squirted it over Ben's ass crack. I liberally applied to my cock as well, and then rubbed my cock through Ben's crack, spreading the lube over both.

Ben shuddered, but held his ground stubbornly. The cool night breeze blew across us and I imagined the feeling must be delectable on his sore, lubed up, ass. I pressed the tip of my cock into his puckered hole. I'd been fucked in the ass before, so I was gentle and slow as I worked my way in, knowing just how painful it could be if I moved too quickly. There was no hurry, after all.

It was rather audacious, actually, to slowly take my time when we were technically in public. I reveled in that delicious feeling of being perverse. It was only heightened that I knew most people wouldn't quite understand the allure of pegging a man in a dress. It wasn't like we were up to good old fashioned fucking out here. That made the thrill of possibly being caught so much more intense.

I felt Ben tremble as I finally slid all the way in. I held myself pressed into him for a moment, then slide out, slowly again. I squeezed more lube on my cock and Ben's ass, then slid into him again. I started slowly, rocking my hips back and forth, then picked up speed, until I was sweating with the effort of fucking Ben.

In front of me, Ben was grunting with the effort of holding his ass still for me, his arms shaky and his breathing rapid. When I sensed the end of my stamina coming near, I wrapped my hands over Ben's skinny hips and amped up my speed.

"Come for me," I ordered him.

In a crescendo of the physical sensations, the buildup of anticipation that'd been growing throughout the evening, and the psychological effects of my words, Ben came. I didn't stop fucking until his legs wobbled and he fell forward on his limp arms into the side of the car.

Relieved that things had gone about how I'd planned, I pulled out. I was unsteady on my feet, as well, as I moved next to the car and leaned my back against the frame. Next to me, Ben had his cheek pressed into the cool metal, his mouth open and gasping. I felt like kissing him, but he hadn't earned that much vulnerability from me, yet. Instead, I planted a chaste motherly peck on his sweaty forehead.

"Good job," I said. "Gold star effort."

Laughing to myself, I pulled the packet of stickers I'd bought from my back pocked, peeled off a gold star, and pressed the sticker onto the side of Ben's cock cage, avoiding the front which was still dripping with his semen.

"Thank you," Ben breathed heavily, "Ma'am."

I unbuckled my cock, which I'd strapped on outside my pants and dropped it into the bag it had come in, in the car. Ben dropped to his knees next to me and I frowned down at him.

"Please... Please, may I lick you? I want to give you pleasure too," Ben begged from the ground.

"No. You haven't earned it yet," I told him, not even sure why I felt a stirring of disquiet at the idea of opening my legs to this young man.

I loved receiving cunninglingus. I adored it. It was the only way I orgasmed. Yet, when presented with this golden opportunity to indulge, I was hesitant.

Ben's body deflated under my criticism and I felt unnecessarily cruel. This time, I didn't feel the thrill of power, the joy of control given and accepted. No, now I just felt like I'd kicked a puppy.

I sighed and reached down to run my hand through Ben's soft brown hair. I let my hand trail over his cheek and he leaned into my touch, reminding me of a dog desperate for the affection of his master. No, his mistress, I corrected myself.

"You did well, tonight," I assured him. "I can either drop you off at your place now, or you can come home with me."

I felt Ben's body tense with excitement as I mentioned the possibility of going home with me.

"If you go back to your place, we can do something like this again, but if you go with me, you'll be my pet," I warned him. "You'll sleep on a dog bed on the floor next to my bed, you'll eat from a dish on the floor, drink from a bowl, and if you survive the weekend, you can lick my pussy."

Ben nodded.

"Wait," I cautioned him. "Get in the car, sit for a bit, and think carefully while I head out of here. I'll ask you again. Be sure of what you want, Ben."

Ben was quiet as I drove. I waited about ten minutes, then asked again, "Where should I take you, Ben?"

"I want to go home with you, Ma'am," he replied, voice clear and firm.

Heat bloomed in my chest and my nipples tightened with excitement. Most men, I knew, would have backed out of this long before now. They would have balked at the cock cage alone. But Ben had taken that in stride, accepting it and he hadn't even asked yet when he might be allowed out of it. I mused as I headed home that Ben was quite a marvelous find. And for some reason, he'd chosen me.

By the time I pulled into my garage, Ben was sleeping. It wasn't surprising, after what I'd put him through in terms of emotional and physical stress. I shook his shoulder gently until he woke up. Ben smiled sleepily up at me, and I felt something unexpected stir in my chest. It was a feeling I'd been quite sure I'd never feel again, something like that tender caring that signals a beginning to love.

I sucked in a breath, and pulled away from Ben. He frowned at my sudden retreat, eyes crinkled with worry.

"Leave your heels and dress in the car and follow me," I said, my voice cold as I suppressed my brush with real emotion.

Ben, sensing the shift in my mood, was quiet and kept his head submissively aimed at the floor as he followed me. I didn't have a big house, I had spent my money on the plot instead, the expansive ten acres that insulated me from neighbors with the grove of pine trees that gave me natural privacy all year long. The house though, was small, more like a cabin.

I pointed out the giant pillow I'd bought earlier that week, with my brain full of crazy ideas I didn't think would actually happen. But, already, things had progressed much further, and faster, than I'd imagined. I blamed Ben for his eagerness, and his willingness to experiment.

"You need a bath before bed," I said, waving Ben into the attached bathroom.

He walked in and waited for me, in his assigned position, still remembering, even sleepy as he was. The sight of that, that quiet acceptance and attention to detail, aroused me. Slipping into the room, I turned on the water, checking the temperature before I plugged the bath and let it fill. I then turned my attention to my naked young man,.

I sat on the toilet and grabbed his cock cage, pulling him towards me. I entered the combination and slid it off of him. I'd read that it didn't really need to be removed for cleaning, but I wasn't interested in taking chances with the health of my new pet's penis. The penis that started growing as soon as it was free.

I smiled as it twitched up, waving at me, "Get in the bath," I instructed.

Ben obeyed, smoothly lowering himself into the tub. I kneeled next to the bath, just as I had a hundred times before when I'd had a dog. Then, I started with his head, shampooing and washing his hair. I had left his collar on, and I washed his neck gently under and around it.

"Close your eyes," I instructed, as I cleaned his face.

And then, I moved down his body, to his shoulders, arms, chest, and then lower still. I moved past his cock and lathered soap on his thighs and calves and feet instead. And then, when it was almost the only place left to clean, I rubbed my hand into his ass crack, cleaning the hole I'd just claimed. I saved the best for last, gliding my soapy hand up Ben's balls and then along his cock.